The ’00s will likely be remembered as the era “alternative comedy” broke. After the boom and bust of stand-up in the ’80s and the distinctly Seinfeld-ian ’90s, a new generation of smartasses arrived to stretch the limits and help redefine it. David Cross proved stand-up didn’t need to be performed in traditional two-drink-minimum comedy clubs. Neil Hamburger created comedy that’s funny because it’s so incredibly not funny. Mike Birbiglia went from traditional stand-up to a storytelling format that became one-man shows. Scharpling & Wurster reignited the radio comedy of days gone by. And Tenacious D and Flight Of The Conchords showed that musical comedy can exist in the post-ironic age. That said, it wasn’t all envelope-pushing; plenty of comics released fantastic old-fashioned comedy albums—and even as the younger generation took hold, old pros like George Carlin and Chris Rock released some of their finest work. The A.V. Club looked back on the aughts and picked our favorites.

Two months after two jetliners dive-bombed a gaping hole into his native New York City, George Carlin took the stage at New York’s Beacon Theatre on live HBO and opened with this: “You know somethin’ people don’t talk about in public anymore? Pussy farts!” Carlin had a live wire to a nation at its most vulnerable, and he wasn’t about to let us stay all moony and soft. Complaints And Grievances sounded like a tremendous warning shot, and the warning went like this: The alert curmudgeon of 1999’s You Are All Diseased would dig his finely manicured claws of vulgarity into humanity’s faltering conscience until the bitter fucking end. There’s no pompous sense of mission to keep Carlin from tearing through a lengthy discourse on picking mysterious objects from your ass (“Honey, come here! Want a couple of hits off of this? Did we eat at Kenny Rogers’ restaurant again?”) or bitching about the rise of “soft” names. (“I’ll bet you anything that 10 times out of 10, Nicky, Vinnie, and Tony will beat the shit out of Todd, Kyle, and Tucker.”) Key track: Carlin ends Complaints And Grievances with “Why We Don’t Need 10 Commandments,” perhaps the most cosmically daring moment in the history of comedy and/or live television: He reduces the 10 Commandments to two, then challenges God to prove His existence by striking the audience dead. (Scott Gordon)

Todd Barry may well be the least excitable comic on this list, and with good reason. It takes a certain meticulous touch to construct such mini-snowglobes of sarcasm as the 55 tracks on his first album, 2001’s Medium Energy. Most of them cram entire episodes of satire into less than a minute, like “Bands Reuniting,” in which The Eagles announce they’ll be getting back together to “knock some stuff around” at Giants Stadium, “then leave in nine separate limousines.” Medium Energy is also a lesson in how fun it can be to craft thoroughly depressing images: “Those restaurants in Chinatown just don’t make hot-dog-fried rice the way I like it,” Barry says in a bit about purchasing a wok to make his own “mediocre Chinese food”; he gets another bit (“Check With Meal”) from his habit of eating out alone. Key track: “Neck Tattoo” (which clocks in at a comparatively whopping 2:32) stands with the rest of the album’s bits in its sly observations. (“‘Hey man, you forgot to notdo that, ya big scary piece of shit.’ That’s the way I talk to big guys with neck tattoos.”) Then it expands into the full Todd Barry package, complete with weird crowd interaction and perverse egotism: “Then they roll over and they go, ‘Holy shit, it’s Todd Barry peeing on me. This is the best Valentine’s Day Ever.’” (Scott Gordon)

Yes, the D was funnier when it was just Jack Black, Kyle Gass, two guitars, three chords, and several F-words. And, sure, some of the duo’s best songs (“Cosmic Shame,” “Sasquatch”) didn’t make it to this self-titled debut. But Tenacious D remains a surprisingly credible rock record that holds up even after the jokes about Cleveland steamers and cock push-ups wear out their comedic value. Which is good, because while Black’s endless mugging is a little too familiar now after a decade of mostly forgettable movies, his relentless vulgarity and shameless self-indulgence make him an ideal hard-rock frontman, with or without a dose of irony. Key track: “Fuck Her Gently” shouldn’t be relegated to the comedy-album ghetto—it’s one of the decade’s best love songs, period. (Steven Hyden)

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Neil Hamburger, Laugh Out Lord (2002)Making “painfully awkward” sound like a walk in the park, Neil Hamburger has skirted the fringe of both the comedy and indie-rock worlds for years. But Laugh Out Lord isn’t just a monument to his staying power; it shows exactly how willfully and depressingly unfunny comedy can get, while still making people laugh. On Lord, Hamburger—the homeless, hapless, neo-Borscht Belt persona of Gregg Turkington—subverts the overcompensating swagger of the typical neurotic comedian in favor of something much more glum and bizarre, including dips into excruciating solipsism and 9/11 jokes cracked way too soon. Riddled with off-target pop-culture jabs, canned heckling, horrible timing, phlegmatic throat-clearing, and the occasional onstage nervous breakdown, Laugh Out Lord shows Hamburger to be a true meta-comic for our age.Key track: “Popular Music,” in which Hamburger makes homophobia sound more like Dada than hate speech. (Jason Heller)

The explosion of so-called “indie comedy” in the ’00s can be traced pretty easily to David Cross. In the aftermath of 9/11, as the nation’s smartasses were reeling with conflicted feelings—horror about what happened, but trepidation about the dangerous and less dignified responses—Cross ditched comedy clubs and toured music venues in early 2002. September 11 and what followed created a deep comic well that Cross revisits several times over the course of the two-disc album that came from that tour. But it’s not all mocking Bush (“We’re all treating him like he came in third place in the Special Olympics”) and living in New York during the attacks. (“If Gabriel wants to Rollerblade, Gabriel Rollerblades. So fuck you, Mr. Osama bin Jerkhead!”) Cross also gets personal, talking about his Southern upbringing (another favorite topic), his family, Rickey Henderson, and more. Shut Up You Fucking Baby! found Cross at the height of his powers, and it set the stage for similarly minded comedians.Key track: “Playing Pool With My Wife” (all the titles are non sequiturs), where Cross offers a couple of anecdotes about living in New York during “the week football stopped.” (Kyle Ryan)

An overdose in 2005 cut Mitch Hedberg’s career short, just when it seemed to hit its stride. He released only two albums during his lifetime, Strategic Grill Locations and Mitch All Together. (A third, Do You Believe In Gosh, came out last year.) Hedberg’s simple one-liner style most closely resembles Steven Wright’s, but less bizarre and more focused on daily inanities (“You know crazy straws that go all over the place? These fucking straws are sane”) delivered via Hedberg’s unmistakable stoner-guy drawl. It’s 17 tracks of one-liners and non sequiturs, with Hedberg commenting on his own act and often laughing at his screw-ups. It’s breezy, charming, and funny, which makes it an even bigger shame that there won’t be more of them.Key track: “Houses” finds Hedberg riffing on the dullest thing, but making it funny: “I bought a two-bedroom house, but I think it’s up to me how many bedrooms are in it, don’t you? This bedroom has an oven in it. Fuck you, real-estate lady!” (Kyle Ryan)

Festooned with images of anonymous boob-flashing ladies, Dave Attell’s 2003 album allows snobbier listeners to enjoy the sleazy aftertaste of every comedy-club hack out there without actually feeling stupid. The track list even reads like the most clichéd stand-up set possible: “Flying,” “Homophobic,” “Condoms,” “Drugs,” “Dick Jokes,” and so forth. Yet even when he’s talking about Girls Gone Wild, Attell plays his bar-goon persona to deceptive advantage: “I like to play it backwards, ’cause then it looks like the girls have learned their lesson.” Maybe that element of surprise is what keeps Attell in charge of the unruly-sounding crowd. Or maybe it’s the sense that he’s right down in the seedy side of life with his audience, but makes it sound wondrous: “If I need directions, I’m not askin’ a man with one tooth. I’m asking a man with one leg, because he definitely knows the easiest way to get there. You won’t be hoppin’ fences, neither.” Key track: “Drinking Tips” proves that one of comedy’s oldest strip-mines still has a few nuggets to spare, and the advice is indeed sound. “Never get drunk when you’re wearing a hooded sweatshirt, ’cause you will eventually think there’s someone right behind you.” (Scott Gordon)

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Patton Oswalt, 222 (2004)The block of granite from which Patton Oswalt sculpted his exquisite debut, Feelin’ Kinda Patton, is a sprawling—129 minutes over two discs!—drunken mess of hilarity. Yes, some bits fall flat (the opening comparing drug laws to playground rules doesn’t really catch on), and the best parts made it onto Feelin’ Kinda Patton, but the full version gives Oswalt room to explore funny tangents, and his off-the-cuff remarks often match his prepared material for laughs. The disc also features early versions of bits that would appear on the also-amazing Werewolves And Lollipops, and elsewhere in Oswalt’s act. Key track: Each disc only has one track. Take your pick and settle in. (Kyle Ryan)

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Eugene Mirman, The Absurd Nightclub Comedy Of (2004)Eugene Mirman could almost trick a crowd into believing that he scribbles out his comedy bits during regular noontime wake-and-bakes, but they’re actually remarkably well-crafted. His 2004 debut is the finest introduction to his peculiar comic language. He might agree: As of this year, Mirman’s sets still included such signature bits as this: “A lot of people think that kids say the darnedest things… but so would you if you had no education! You’d just be like, ‘I am bike cheese!’” Mirman takes childlike joy in ambushing life’s most dull, mundane alleys, and that gives him incredible freedom. His ear for the silly and the abrupt can transform seemingly ridiculous subject matter (the movie Teen Wolf, height requirements for theme-park rides, alchemists getting beat up by knights) into a chance to make words collide like drunken bumper cars: “I’m trying to make this candy into karate! Or whatever alchemists did that was more reasonable…”Key track: The easier something is for most people to ignore, the more potential it holds for a Mirman-style attack. “Shapes For Sale” questions ads that simply shill for entire categories of things (like pork or chicken) by introducing a campaign for shapes. “This is a heart: ‘I am a triangle with an ass on top. Please help!” (Scott Gordon)

As a product of the hip-hop generation, Chris Rock has internalized the staccato, aggressive rhythms of rap. There’s a foul-mouthed musicality to his delivery, a pugilistic poetry in the way he circles around punchlines, then swoops in for the kill. On Never Scared, the hilarious CD companion piece to his 2004 stand-up special, Rock discourses darkly on Michael Jackson and the difficulties of being a hip-hop apologist in the age of Lil Jon, but he saves his darkest, most penetrating insights for the special hell of marriage, from having well-meaning wives arrange “play dates” for their emasculated husbands to the agony of married-people dinner parties featuring “six neutered adults.” Rock’s hip-hop sensibility extends to littering the disc with skits that wear out their welcome the first time around, but the odd skippable track is a small price to pay for such trenchant wit. Key track: “Marriage,” of course. (Nathan Rabin)

Outsiders may view it as a lack of quality control, but the way some of the decade’s best comedy records splay out over multiple discs is far more indicative of the casual, inclusive nature of the alt-comedy boom. This take-home version of Eugene Mirman and Bobby Tisdale’s sorely missed (but occasionally resurrected) showcase spans three CDs and one DVD, capturing experimenting veterans (Jon Benjamin brings David Cross onstage as a horrifying OB/GYN), comics testing new material (much of Mirman’s first-disc set would end up on his En Garde, Society), and breakthrough larfs from young turks like Demetri Martin and Aziz Ansari. Ansari’s M.I.A. references won’t age well, but Invite Them Up ought to stand as a document of the past decade’s changing-of-the-vanguard in American stand-up.Key track: Jon Glaser’s contribution to disc one, an epistolary telling of his father’s fictional tenure in ZZ Top. What begins as a riff on storytelling stage shows like The Moth and Mortified quickly devolves into a list of rejected names for the band (The On Top Of Old Smokeys; TT Zop; When The Red, Red Robin Goes Top, Top, Topping Along) and a trashing of the band’s signature beards, underlined by the younger Glaser’s deadpan. (Erik Adams)

The small, insular world of brainy radio comedy changed forever the night drummer extraordinaire Jon Wurster called Tom Scharpling on New Jersey’s WFMU pretending to be Ronald Thomas Clontle, the author of a comically ill-conceived, nonexistent music guide and “ultimate argument settler” called Rock, Rot & Rule. Since then, Wurster has been calling into WFMU as an endless array of deluded, aggressive, and hilarious characters. Hippy Justice, the duo’s magnum opus, collects six of those genius routines, including “Hippy Johnny,” about a tie-dyed tyrant who runs his pseudo-progressive business as a cross between the Manson Family ranch and a 19th-century sweatshop, to “Timmy Von Trimble,” a succinct bit about a two-inch-tall racist created by bigoted scientists. In the parlance of radio jocks, it’s all killer, no filler—and a wonderful introduction to two of the sharpest, most consistent minds in comedy. Key track: “Old Skull,” a genius routine about a creep who reunites prepubescent punk Old Skull as a New Age jazz combo. (Nathan Rabin)

As part of the cabal of Mr. Show alumni and the Comedians Of Comedy, Brian Posehn runs with a group that tends to attract a devoted, nerdy fan base—and he may be their king. He’s tall, gawky, and goofy-looking, with a voice like Frank Oz and a devotion to metal and Star Wars. Any nerd in the audience can look upon him and have hope for success in life, as Posehn has made a good living talking about metal, getting high, and other silliness. Live In: Nerd Rage has him expounding on those and other hilarious subjects—including a killer bit about his dog licking his wife’s vagina while she was on the toilet—and even performing a song called “Metal By Numbers” that mocks the metal-song template. Key track: “Nerd Rage/The Mattress Story,” in which Posehn describes his still-lingering hatred of jocks, and how it ends up reflecting poorly on him. (Kyle Ryan)

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Paul F. Tompkins, Impersonal (2007)Paul F. Tompkins fills out his dapper, loud suits with a mischievous grin and a megawatt sense of superiority on Impersonal, a collection of some older stand-up material. A bit like Wile E. Coyote speeding over a cliff’s edge but enjoying it, Tompkins launches epic satiric attacks on targets few people would bother thinking about, much less mocking. Perhaps the most ridiculous is his arch tearing-down of Sesame Street’s inadequate Spanish-language instruction (“They needn’t have bothered!”), or a satire on those who died in the Irish Potato Famine. (“Are these the pickiest people, or what?”) But the storytelling is there, as is Tompkins’ talent for needlessly stretching a bit far past its breaking point and making people love it.Key track: “Peanut Brittle” is the comedy equivalent of an absurdly long drum roll. As Tompkins puzzles over a new modern line of prank peanut-brittle cans, he takes every miniscule opportunity to build up the premise that peanut brittle is the most common thing on earth. In typical Tompkins fashion, the bit only gets funnier as it plows on and on. (Scott Gordon)

Prior to this album, genial, disarming comic Mike Birbiglia certainly wasn’t a slouch (see Two Drink Mike), but his decision to take up comedic storytelling feels like a light bulb turning on. Birbiglia took tales garnered from his family, his childhood, and cringe-worthy stand-up gigs, and retold the shocking details in the calculated style of a master campfire storyteller, peppering them with conversational asides. At a cancer benefit, Birbiglia decided to tell some cancer jokes, which were met with groans. His hilarious, instantly regretful response: “I know… I’m in the future also.” Thus stories about porn viruses and inadvertently insulting blind people feel a lot more personal, and the laughter comes from a place of catharsis on Birbiglia’s behalf. He’s since gone on to open a successful Off-Broadway show called Sleepwalk With Me, containing similarly told stories about his sleepwalking disorder, but it’s on My Secret Public Journal Live that Birbiglia seems the most eager to play with the new format—and the surprising, compelling results speak for themselves.Key track: “Joe Bags,” about a summer job where he’s warmly welcomed because his brother used to work there. Turns out, the guy his co-workers are thinking of isn’t his brother. (Steve Heisler)

David Koechner and Dave “Gruber” Allen have stumbled onto a nearly perfect dynamic for a musical comedy act: As the rowdy T-Bones and the dropout hippie Naked Trucker, the duo plays dimwitted but pseudo-intellectual long-haul drivers on the same rig, heightening the absurdity by singing about their love of porn, Tex-Mex, and the best truck stops across this great land. There’s a heavy dose of rebel irony injected into this disc via a truly unexpected hip-hop cover (“Gin & Juice” ends with a rabid shout-out to the Tennessee Valley Authority and hillbilly hip-hop), but the pair’s slow-burning charm and unabashed silliness makes the nearly hourlong live disc a steady stream of giggles. Live At The Troubadour bears repeated listens thanks to the pair’s dramatic chops, and it doesn’t hurt that both comedians are actually competent musicians and singers—though Koechner prefers to jaunt around the stage while hitting a jug with a paint stick.Key track: “Hobo Holiday (2 Dollars)” (David Wolinsky)

Zach Galifianakis, Live At The Purple Onion (2007)Zach Galifianakis has never released a comedy album, but any talk of stand-up genius in the ’00s would be incomplete without him. So if you must, close your eyes and pretend that his lone purchaseable release, the DVD Live At The Purple Onion, is a CD, but don’t ignore it. Not only does it feature some of the bearded actor’s confrontational stand-up—complete with long portions in which he accompanies his jokes with light piano—but also a mini-documentary interspersed throughout in which his rube of a “twin brother,” Seth, is interviewed by NPR’s Brian Unger. It’s mad genius.Key scene: When “Seth” breaks down crying and admits that he and Zach only have two things in common—a fondness for Funyuns and a particular Fugees song. (Josh Modell)

You wouldn’t guess it based on his other work—writer-director of Pootie Tang, sweet-natured guest star on Parks And Recreation, the list goes on—but affable comedian Louis C.K. might be the rawest stand-up working today. The reason he’s so effective—and he gets better with every release—is that C.K.’s act is grounded in reality, but he magnifies his darkly funny side to ridiculous-yet-believable proportions. On Chewed Up, he covers the basics—the differences between men and women, the annoyance of having children, “the n-word”—but does so with relish and no fear. Like George Carlin in his day, C.K. pushes the barriers of language; also like Carlin, he isn’t for everyone.Key track: “The Diaper” includes C.K.’s feelings about kids and sex: “I had no idea that my relationship with a vagina was going to be cleaning shit out of a tiny one several times a day.” (Josh Modell)

Initially earning a cult through a live show in which they sat on stools, played acoustic guitars, and never cracked a smile while performing songs that punctured every cliché of romantic folkies and lusty R&B men, Jemaine Clement and Bret McKenzie took to the recording studio like a Rhymenoceros takes to a Hiphopopotamus. The first season of their HBO show was written around these songs (not the other way around), and they tweaked the arrangements just enough to make their debut something people can still listen to once they’re done laughing. Even a cursory listen reveals that Clement and McKenzie are far more than simply “New Zealand’s fourth most popular folk-parody duo.” They deserve to be at least third—maybe second.Key track: “Business Time,” which proves they can turn just about anything into a “sexy dance.” (Michaelangelo Matos)

Former Simpsons and Ben Stiller Show writer Dana Gould is a comedian’s comedian and a formative influence on better-known stand-ups like Patton Oswalt, who has sung his praises far and wide. Listening to Let Me Put My Thoughts In You,it’s easy to see why he inspires such admiration and devotion in his fellow comics. Here, Gould concedes that, like his father before him, he essentially has two emotions, “rage and suppressed rage”: He’s an agitated everyman railing impotently against an insane world and the million little indignities and humiliations that constitute everyday life. Key track: “Let’s Argue!” offers an acidic take on the domestic combat of marriage. (Nathan Rabin)

Chris Rock is brilliant and often daring, but even he wouldn’t be willing to describe Michelle Obama as a “real nigga” who “smells like Motions hair conditioner and cocoa butter.” On 2009’s It’s Pimpin’ Pimpin’, Katt Williams goes there, while also defending Michael Vick, Britney Spears, and the tiger that mauled a kid who wandered into its cage. The 73-minute CD slips a bit at the end, but Williams’ riffs offer a perspective people may not hear unless they see him at one of the 6,000-seat venues he routinely sells out—“urban” theaters also frequented by gospel shows and the plays of Tyler Perry. Like a trip to a Harlem barbershop, Williams’ best routines make people laugh, think, feel a little uncomfortable, and reach for Google to look up some of the references.Key track: “Scared Of Rope,” on which Williams says of Flava Flav, “certain niggas, you don’t expect to learn nothing from.” (Spoiler: He does.) (Brett Singer)

For ages, it’s been far too easy for stand-up and sketch comics to thrive on acts that are at least 50 percent hyperactivity. (Case in point: Dane Cook, or Saturday Night Live’s Spartan cheerleaders.) So how come none of them can keep up with Maria Bamford’s verbal pinball? Bamford uses her barrage of exaggerated voices to chip her way toward some pretty elusive ideas and trick the brain into thinking about some pretty weird shit. That’s what Unwanted Thoughts Syndrome is all about: dwelling on the weird tension of planning lunch with your office mates, phone messages from Baby Jesus, performing as a Star Trek character in the mall. These aren’t impressions, they’re complete scenes, and they all sink in slowly and uncomfortably, in spite of Bamford’s twitchy energy. Key track: “Vision Board” probably boasts the most voices per minute, and the craziest sequence of subject matter. The track begins with a little arts and crafts, and ends with a bit on attending an overly emotional seminar on pugs: “I cannot tell you how many times I’ve found the limp, lifeless body of a Yoda or a Dr. Snuggles hangin’ off the adjustment lever of a Lay-Z-Boy.” It turns stand-up into hallucinatory drama, yet the laughs are as uncontrollable as they are unsettling. (Scott Gordon)